Traveling to Hawaii with a big group is a fun time. Whether you’re heading here with friends or for a family reunion, you know the trip is going to be memorable. But it can be a little tricky when you’re traveling with a group of eight or more. You want to find a place big enough to fit everyone with amenities that will make things comfortable. 

To help, we’ve rounded up the 10 best Maui vacation rentals for large groups. These places not only fit eight or more guests, but they’re also in resort or rental communities where you can book multiple units. So you can choose to either stay together or get your own spaces. Plus, we’ve included four large homes that will fit 18+ guests in case you want your large group to stay together under one roof. 

Ready to book your trip? Here are our 10 favorite Maui vacation rentals for large groups. 


1. Kahana Outrigger

Kahana might be one of the best-kept secrets of the west side. Just north of Kaanapali and south of Kapalua you can find the Kahana Outrigger, a low-rise condo development with just 16 townhomes. Each of the townhomes are three-bedroom, making it ideal for a group to stay together. 

Have a larger group? It’s easy to book two or more townhomes together. 

Let’s talk about the location. Kaanapali has a great beach, but when resorts are running at full capacity, you have thousands of people in the same space. Kapalua is much less crowded but it’s also much more expensive. If you’re looking for a place for your large group on the west side that is on a quieter beach but doesn’t cost as much as Kapalua, this is a great spot. You’re also just 15 minutes north of Lahaina so trips to visit the town are easy. 

The townhomes in the Kahana Outrigger are spacious (average 1,500 square feet) and sleep 6-10 people. They’re all located steps from either the beach or the pool, perfect for days that you just want to stay around the condo. Plus, they have some of the best ratings on VRBO.

Check out the Kahana Outrigger listings on VRBO

Kaanapali Maui vacation rentals for large groups

Ka’anapali Beach is just south of Kahana, making Kahana a great place for large groups to stay.


2. Honokeana Cove

Another gem of the west side, Honokeana Cove offers a small condo community right on a cove. The sunsets are spectacular, but a quick note: there is no beach directly in front of the condos. It’s a rocky cove full of turtles (beautiful!), but if you have kids and want to hit the beach easily, it’s a bit of a walk to Napili Bay. Still manageable, but with toddlers, you might find it challenging. 

Staying at Honokeana Cove, you’re a quick five-minute walk to the famous Napili Bay, a short 5-minute drive to Kapalua, and a 15 – 20 minute drive to Lahaina. 

In Honokeana Cove you’ll find condos up to a maximum of three bedrooms. Need more space? It’s easy to book multiple condos on VRBO to accommodate your group. Plus, I think this is one of the best-priced condo rentals you’ll find on the island for big groups

Explore Honokeana Cove rentals on VRBO


3. Honua Kai

If you’re looking for more of the big resort experience, the Honua Kai offers studio to three-bedroom condos on 38 beachfront acres. It’s like a big hotel, with 600 rooms, resort-style pools, a concierge, and restaurants on-site. Some of the three-bedroom units are large — nearly 2,000 feet and can sleep 10 people.

Honua Kai is located on the beach in North Kaanapali. Slightly different from some of the other options on this list, you can book a room at Honua Kai either directly through Outrigger or from a private owner on VRBO. 

And if you have a group of up to 24 people going, there is an option on VRBO to rent 3 separate but neighboring villas within Honua Kai. Perfect for multiple generations or multiple families who want to stay very close together, but still have their own space.

Check out Honua Kai on VRBO or on Outrigger


4. Montage Kapalua

If I was traveling to Maui with a large group and had an unlimited budget, I would absolutely stay at the Montage Kapalua. Hands down. 

This luxurious property is located on a beach near Kapalua Bay, approximately 25-minutes north of Lahaina. Yes, it’s a little further away from the action, but I think that’s the draw. The Montage Kapalua is pure luxury.

The Montage Kapalua offers one to four-bedroom residences set on a vast, ocean-front landscape. Add in upscale restaurants, a top-notch fitness center (yes, they have a Peloton), a kids club, pool bar, and a spa, you may never want to leave the resort. 

Book a luxury stay at the Montage Kapalua Bay

West Maui vacation rentals for Large groups Map


5. Napili Gardens

We love Napili. We love Napili so much, we even made a video about staying in Napili. So we had to include Naili Gardens on our list of vacation rental options for large groups. 

Napili Gardens offers a quiet rental experience with three-bedroom townhomes. If you need any more space, they even have a double condo rental option, where you can rent two condos at once for a total of six bedrooms

Napili Bay is one of the best beaches on Maui and these townhomes aren’t right on the beach, but are just a quick walk across the street. And each townhome features a small, private lanai. Napili is a great beach for families, for snorkeling, and stand up paddle (SUP), with rental shops right on the bay. You’re also just a quick 15-20 minute drive to Lahaina for additional restaurants, shopping, and nightlife. 

You can view and book the townhomes at Napili Gardens on VRBO

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6. Koa Resort Kihei

The Koa Resort is located centrally in Kihei and is probably the most cost-effective spot on our list. Here you’ll find spacious one to four-bedroom townhomes. Need more space? You can book additional rentals within the resort.

The resort is spread over five acres. Here you’ll find two tennis courts, a jacuzzi, a large swimming pool, hot tub, and shuffleboard. The resort isn’t right on the beach, but it’s a quick five-minute walk. 

Kihei is very centrally located on Maui and you’re just a 10-minute drive to Wailea or a 25-minute drive to Lahaina. 

You can book and view the condos and townhomes on VRBO

South Maui Vacation Rentals for Large Groups Map


7. Papakea Resort

Just north of Kaanapali beach, you’ll find Papakea Resort. Here you’ll find rentals from as small as a studio to as large as a three-bedroom (with a maximum occupancy of 10). This is a great option for groups that want to book a number of different rooms of varying sizes within the same resort. 

All rooms come with private lanais and a washer and dryer. You’ll also have access to two swimming pools, two jet pools, a tennis court, putting greens, picnic areas with BBQs, pickleball, and shuffleboard. 

Visit the Aston Hotel site to learn more and make a reservation


8. Westin Nanea Ocean Villas

Located on North Kaanapali beach is the Westin Nanea Ocean Villas. These are resort-style condos, giving you the amenities of a nice hotel with the space of a vacation rental. You’ll find one to three-bedroom villas, up to 1,470 square feet that are perfect for nine adults.

The resort has a main pool as well as two plunge pools. You’ll also find a gym, on-site dining that includes both a pool bar and market to stock your condo. Plus, a children’s splash pad to keep little ones busy and cabanas by the pool. There’s also a Westin Kids Club for kids that want additional space to play. If you have a very large group, for a wedding or a large family reunion, they offer tools to make group booking easier. 

Visit the Westin site to learn more and book a rental


9. Ho’olei Villas 

The luxury resort in Wailea, the Grand Wailea, owns the Ho’olei Villas, an accommodation option that blends resort amenities and residence living. 

At the Ho’olei Villas you can rent two or three-bedroom villas that are huge, ranging from 3,200 to 4,000 square feet. On the villa property, you’ll find a pool with a 19-foot waterfall, a spa, a fitness center, a concierge, and multiple restaurant options. A quick note on the pool situation: though these residences are affiliated with the Grand Wailea Resort, you won’t have access to the pool at the Grand Wailea Resort. If you’re hitting the pool, you’ll need to use the one located at the Villas. 

These villas are located in the center of Wailea with beach access across the street. 

Rentals can be booked either through the Waldorf Astoria website or through VRBO

Note: you don’t have access to the Grand Wailea pools, though the Ho’olei Villas has their own.

grand wailea Ho’ olei Villas maui vacation rental large group

The Grand Wailea is luxury living on Maui.


10. Wailea Beach Villas

Another luxury property in Wailea, the Wailea Beach Villas are ocean-front and offer more amenities than you’ll find at a normal hotel. Located next to the Shops at Wailea, the Wailea Beach Villas offers 2-3 bedroom villas, up to 4,200 square feet. Some of the units are located directly on the beach, so if that’s important to you be sure to book correctly. 

At the resort, you’ll have daily housekeeping services, use of a Tesla resort car, a gym, two pools, a concierge and bellman, 24-hour security, and massage services. This resort is centrally located in Waiea, so you can walk to other resorts and shopping very easily. 

You can book through the Destination Hotels website or on VRBO. 

wailea beach maui perfect for large group vacation rentals

Wailea Beach on Maui has good vacation rental options for large groups around it.


Houses on Maui that fit 18+ People

1. Kapalua 7 Bedroom Home for 25+ People

With the Montage, the Ritz, and a famous golf course, Kapalua means luxury. So it’s not surprising that a stunning, custom built vacation home that is available for rent here. With seven bedrooms, a private pool, and a rooftop lounge, you might be tempted to never leave. But you should venture out because this home also has you just steps from the beach. The waterslide will keep kids and adults busy while the indoor/outdoor flow makes it easy for everyone to mingle casually. If I were hosting a big bash, reunion, or wedding on Maui, this is the first spot I’d pick.

Check out all the details of this spot on VRBO.


2. South Maui 8 Bedroom Luxury Villa

Have a party of up to 18 people? This south Maui gem is calling you. With 8 bedrooms, this ocean front private home is steps from downtown Kihei but still offers unobstructed ocean views. You can walk to Kihei restaurants and the supermarket and then retreat back to your home and the beach. Technically this home can be split into three different units, but as of publishing the owner is renting the entire home to one group at a time. There’s no pool here but you’ll have plenty to keep you busy between the lawn games (and large lawn) and the beach.

See this place for yourself on VRBO.


3. 12 Bedroom South Maui Home

If you’re looking to house up to 24 people under one room but still maintain some separation, this is the spot. This is technically four 3-bedroom villas that are 2,000 square feet each, but you’re not staying in a large resort area. It’s one private building, with multiple living spaces. So you’re together, but a little bit separate. It’s available to host weddings of up to 65 and is beachfront while still being walking distance to Kihei. There’s also a pool and the spaces are decked out with high end furnishings and finishes.

See if your dates are available on VRBO.


4. Up to 32 Guests on West Maui

This might be the largest rental home on Maui. With 10 bedrooms, a bunk room, and multiple pull out couches, this spot makes it easy to find a sleeping arrangement that will work for different groups. It’s close to the ocean, though don’t expect sweeping ocean views. Here you’re just 10 minutes north of Lahaina so you can enjoy being centrally located. You’ll be living the high life in this newly renovated property with a fitness center, movie room, pool, and easy beach access. 

Check out this gem on VRBO


You’ve found the place, now plan the trip

Finding a vacation rental for a large group is no easy task. But now that the hard work is done, wrap up your trip planning with one of our done for you itineraries.

These done for you days will take you around to the best spots on excursion days, so you can make the most of your valuable vacation time. We include beaches, restaurants, hiking spots, and more to make sure you have wonderful days out.

“Just wanted to thank you for the awesome itinerary you have put together. We just got back from our 10 day Maui trip & it was such a great help to my family. We saw and experienced so much. Thank you for putting all of this fantastic travel information out there! For this travel research nerd, I sure do appreciate it!”


Erica Gellerman

Erica Gellerman

I'm the co-founder, with my husband Jordan, of The Hawaii Vacation Guide. We live on Maui with our toddler Henry and our sweet but quirky dog Hattie. I am a planner! I love to plan island-hopping adventures, days out on Maui, and everything in-between. I spend a lot of my time on our SUP and my favorite time of year in Hawai'i is whale season!

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